The first is to cut Ty Wigginton in favor of Yunel Escobar. Torn on this one, because I like Wigginton's power upside in Coors, but his playing time is a concern. I like Escobar this year, but his ceiling isn't as high as Tys. This would be for my CI slot.

The second is to acquire Ryan Dempster. My rotation is not all that great for a 10 team league: Kershaw, Tim Hudson, Brett Anderson, Matusz and Ian Kennedy. Is Dempster > Kennedy? Or should I cut Chris Sale instead (who is currently the setup man and isn't guaranteed the closer gig)?

Without seeing your whole squad, or the cats in your league, I'd drop Wiggy for Escobar and Kennedy for Dempster.If your league counts HLDs (or K/9, etc..), then keep Sale. If not, then I'd consider dropping him instead of Kennedy.